4-Fluorophenol → 3-Bromo-4'-fluorodiphenyl ether

HRID 1909083Notes

Reaction equation

HRID 1909083 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CC(N(C)C)=O.[Cu]I.O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:4]2[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)=[CH:12][CH:11]=1

Participants

8

Reactant 4

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 75605N,N-Dimethylglycine hydrochloride

Product 1

HCID 27786893-Bromo-4'-fluorodiphenyl etherYield 33.6%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-bromo-3-iodo-benzene (1.00 g, 3.55 mmol), 4-fluorophenol (462 mg, 3.59 mmol), N,N-dimethylglycine hydrochloride (149 mg, 1.06 mmol), and cesium carbonate (2.28 g, 7.00 mmol) in DMA was added CuI (66.8 mg, 0.351 mmol). The reaction mixture was heated at 90° C. for 48 h, cooled to rt, and then poured into water and extracted with EtOAc (3×). The organic layers were combined, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound as a colorless oil (319 mg, 32%).

Workup

  1. temperaturecooled to rt
  2. extractionextracted with EtOAc (3×)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-9f126d6ff2d241c58072265d5bde54d5
Source dataset
uspto-grants-2013_12
Patent number
US08598356B2

Reaction notes

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